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PMID: 18489260 Published · ppublish English Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't

Dissecting isoform selectivity of PI3K inhibitors: the role of non-conserved residues in the catalytic pocket.

The Biochemical journal ·Vol. 414 ·No. 3 ·2008-09-15 ·Pages 383-90

Frazzetto M, Suphioglu C, Zhu J, Schmidt-Kittler O, Jennings IG, Cranmer SL, Jackson SP, Kinzler KW, Vogelstein B, Thompson PE

Abstract

The last few years have seen the identification of numerous small molecules that selectively inhibit specific class I isoforms of PI3K (phosphoinositide 3-kinase), yet little has been revealed about the molecular basis for the observed selectivities. Using site-directed mutagenesis, we have investigated one of the areas postulated as being critical to the observed selectivity. The residues Thr(886) and Lys(890) of the PI3Kgamma isoform project towards the ATP-binding pocket at the entrance to the catalytic site, but are not conserved. We have made reciprocal mutations between those residues in the beta isoform (Glu(858) and Asp(862)) and those in the alpha isoform (His(855) and Gln(859)) and evaluated the potency of a range of reported PI3K inhibitors. The results show that the potencies of beta-selective inhibitors TGX221 and TGX286 are unaffected by this change. In contrast, close analogues of these compounds, particularly the alpha-isoform-selective compound (III), are markedly influenced by the point mutations. The collected data suggests two distinct binding poses for these inhibitor classes, one of which is associated with potent PI3Kbeta activity and is not associated with the mutated residues, and a second that, in accord with earlier hypotheses, does involve this pair of non-conserved amino acids at the catalytic site entrance and contributes to the alpha-isoform-selectivity of the compounds studied.

MeSH Terms
Binding Sites Catalysis Catalytic Domain Enzyme Inhibitors/chemistry,pharmacology Kinetics Mutagenesis, Site-Directed Phosphatidylinositol 3-Kinases/chemistry,genetics Phosphoinositide-3 Kinase Inhibitors Protein Isoforms/antagonists & inhibitors,chemistry,metabolism Structure-Activity Relationship Substrate Specificity
Chemicals
Enzyme Inhibitors Phosphoinositide-3 Kinase Inhibitors Protein Isoforms
Authors & Affiliations
10 authors, click to expand affiliations / ORCID
Frazzetto Mark
Australian Centre for Blood Diseases, Monash University, Melbourne, VIC 3004, Australia.
Suphioglu Cenk
Zhu Jiuxiang
Schmidt-Kittler Oleg
Jennings Ian G
Cranmer Susan L
Jackson Shaun P
Kinzler Kenneth W
Vogelstein Bert
Thompson Philip E
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Article Info
Journal
The Biochemical journal
Abbr.
Biochem J
ISSN
1470-8728
Published
2008-09-15
Pages
383-90
Language
English
Region
England
NLM ID
2984726R
PMCID
PMC2820364
Subset
IM
Grants
NCI NIH HHS · R37 CA043460 · United States
NCI NIH HHS · R37 CA043460-26 · United States
NCI NIH HHS · CA 43460 · United States
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